2-Trimethylsilyl-7-hydroxy-1-benzothiophene | 197803-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-Trimethylsilyl-7-hydroxy-1-benzothiophene
• 英文别名: 2-trimethylsilyl-7-hydroxybenzo[b]thiophene；2-Trimethylsilyl-1-benzothiophen-7-ol
• CAS: 197803-67-1
• 化学式: C₁₁H₁₄OSSi
• 分子量: 222.383
• InChiKey: HGDYDIHYUCJQRP-UHFFFAOYSA-N

物化性质

• 沸点：
  335.9±22.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Trimethylsilyl-7-hydroxy-1-benzothiophene 在 四丁基氟化铵 作用下， 以82%的产率得到苯并噻吩-7-醇
  参考文献：
  名称：

  Samanta, Subhendu Sekhar; Ghosh, Sukhen Chandra; De, Asish, Journal of the Chemical Society. Perkin transactions I, 1997, # 18, p. 2683 - 2685

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-diethyl-3-allyl-5-trimethylsilylthiophene-2-carboxamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到2-Trimethylsilyl-7-hydroxy-1-benzothiophene
  参考文献：
  名称：

  Samanta, Subhendu Sekhar; Ghosh, Sukhen Chandra; De, Asish, Journal of the Chemical Society. Perkin transactions I, 1997, # 18, p. 2683 - 2685

  摘要：

  DOI：

文献信息

• Studies in sulfur heterocycles. Part 16. Use of 7-hydroxy-1-benzothiophene in the synthesis of substituted benzothiophene derivatives and tricyclic compounds incorporating a fused thiophene ring
  作者：Sukhen Chandra Ghosh、Asish De

  DOI：10.1039/a904605d

  日期：——

  Heteroatom directed ortho-metallation on N,N-diethyl-7-carbamoyloxy-1-benzothiophene, readily available from 7-hydroxy-1-benzothiophene enabled regioselective substitution in the 6-position. Both 7- and 4-hydroxy-1-benzothiophene were used in the annelation of 5- or 6-membered oxygen heterocycles onto the 1-benzothiophene molecule through sequential Claisen rearrangement–ring closure reactions. The nature of the annelated ring depends upon the reaction conditions.

  异原子定向的邻位金属化反应应用于N,N-二乙基-7-氨基氧基-1-苯并噻唑，该化合物可通过7-羟基-1-苯并噻唑轻易获得，从而实现6位的区域选择性取代。7-羟基和4-羟基-1-苯并噻唑分别用于通过顺序的克莱森重排—闭环反应将5元或6元氧杂环连接到1-苯并噻唑分子上。连接环的性质取决于反应条件。
• Application of directed metallation in synthesis. Part 3: Studies in the synthesis of (±)-semivioxanthin and its analogues
  作者：Sukanta Kamila、Chandrani Mukherjee、Sasanka S Mondal、Asish De

  DOI：10.1016/s0040-4020(02)01599-5

  日期：2003.2

  The synthesis of several analogues of (+/-)-semivioxanthin including five thiophene analogues, using directed metalation are reported. The strategy consisted of the synthesis of functionalized naphthalene or benzo[b]thiophene as building blocks followed by annelation of the pyrone. (C) 2003 Elsevier Science Ltd. All rights reserved.